Hydroxylamine compounds and methods of their use

A compound, hydroxyl technology, applied in the field of new hydroxylamine compounds, can solve the problems of no reported anti-angiogenic activity of hydroxylamines, difficulty in production, etc.

Inactive Publication Date: 2010-03-31
COLBY PHARMA CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, both substances have the disadvantage that both are large molecular weight proteins (240 kDa and 26,000 kDa, respectively), difficult to produce and must be administered by infusion
However, although some nitroxides (e.g., TEMPOL) have shown some anti-angiogenic activity, no hydroxylamines have been reported heretofore to have any anti-angiogenic activity, to have any potency for the treatment of liver inflammation, to have Any potency for inhibiting complement activation, or having any potency for treating complement-mediated or drusen-mediated pathologies such as AMD

Method used

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  • Hydroxylamine compounds and methods of their use
  • Hydroxylamine compounds and methods of their use
  • Hydroxylamine compounds and methods of their use

Examples

Experimental program
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preparation example Construction

[0388] Compound preparation

[0389] General method A: For the synthesis of 3-hydroxy-4-alkyl-1,2,5-thiadiazole or 3-chloro-4-alkyl-1,2,5-thiadiazole or 3-chloro-4 - General procedure for aryl-1,2,5-thiadiazoles

[0390] Aminoamide hydrochloride (20 mmol) was dissolved in 20 ml of DMF. Sulfur monochloride (7.6 g, 56 mmol) was added at 0-5°C over 20 minutes and the reaction was stirred at room temperature for 6 hours. The yellow sulfur precipitate was filtered after quenching the reaction with ice water. CH for aqueous phase 2 Cl 2 Extract (3x20ml). Combined organic phases with MgSO 4 dry. The solvent was removed and the residue was purified on a silica gel column using CH 2 Cl 2 (1 L) as eluent. 4-(2-Methyl-alkyl)-3-hydroxy-1,2,5-thiadiazole was obtained as a pale yellow crystalline solid.

[0391] When amino-nitriles are used instead of amino-amides, 3-chloro-4-alkyl-1,2,5-thiadiazoles or 3-chloro-4-aryl-1,2,5-thiadiazoles are obtained. pass 1 H NMR confirmed the...

Embodiment 1

[0395] General method for the preparation of nitrogen oxides:

[0396] To a solution of t-BuOK in t-BuOH (30 mL) was added TEMPOL in one portion, followed by thiadiazole. The reaction mixture was stirred overnight at room temperature. Water (50 mL) was then added to the reaction mixture. The mixture was extracted with EtOAc (3 x 50 mL). The organic phase was washed with brine (20 mL) and washed with MgSO 4 dry. Solvent was removed in vacuo. The crude product was purified by silica gel column (EtOAc / hexane=1 / 10). After removing the solvent in vacuo, the product (3.0 g) was obtained.

Embodiment 2

[0398] General procedure for the preparation of hydroxylamine HCl salt:

[0399] To a solution of nitrogen oxide compound (~1 g, 5.4 mmol) in 2-propanol (~10 mL) was added in one portion a saturated solution of hydrogen chloride in 2-propanol (~20 mL), and the reaction mixture was stirred at room temperature (1 h to 20 h) or heated to reflux (~2 h) until it became colorless. The solvent was removed in vacuo to give an off-white solid. The crude product was recrystallized from 2-propanol. A white solid (-0.72 g, 3.2 mmol) was obtained. pass 1 The product was identified by H NMR analysis, elemental analysis, IR and mp.

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Abstract

The present disclosure provides compounds that include hydroxylamines of formula (I) or (II), pharmaceutical compositions, and methods for their use. The methods utilize hydroxylamine compounds and / or their pharmaceutical compositions for the treatment of angiogenesis, hepatitis, complement-mediated pathologies, drusen-mediated pathologies, macular degeneration and certain other ophthalmic conditions, inflammation, arthritis, and related diseases and for the inhibition of complement activation.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of US Provisional Application 60 / 891,140, ​​filed February 22, 2007, which is hereby incorporated by reference in its entirety. field of invention [0003] The present invention relates to novel hydroxylamine compounds, pharmaceutical compositions comprising such compounds, and uses thereof. More specifically, the present invention relates to novel hydroxylamine compounds which may possess antioxidant properties and / or free radical scavenging properties and thus may be useful, inter alia, in the treatment of various disease states, disorders or conditions. Background of the invention [0004] Various patents and other publications are referenced herein. The contents of each of these patents and publications are hereby incorporated by reference in their entirety. The entire contents of commonly-owned pending US Patent Publication Nos. 2004 / 0002461, 2005 / 0130906, and 2005 / 0131025 are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/46C07D209/44C07D211/94C07D405/12C07D409/12C07D413/06C07D417/12C07D417/14A61K31/4535A61P17/18
CPCC07D417/14C07D211/94C07D207/46C07D405/12C07D409/12C07D417/12C07D209/44C07D413/06C07C239/12C07C291/14C07C409/12C07D265/30C07D265/32C07D401/04C07D413/12C07F9/59A61K31/133A61K31/15A61K31/40A61K31/4035A61K31/44A61K31/445A61K31/45A61K31/4535A61K31/454A61K31/4545A61K31/4725A61K31/496A61K31/506A61K31/5375A61K31/5377A61K31/675A61P1/16A61P17/18A61P27/02A61P29/00A61P31/12A61P35/00A61P37/02A61P37/06A61P39/06A61P43/00A61P7/02A61P9/00A61P9/10
Inventor 甘希亚姆·帕蒂尔
Owner COLBY PHARMA CO
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